8-(3,4-二氯-苯基)-1,4-二氧杂-螺[4.5]癸烷-8-甲腈 | 65619-34-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 8-(3,4-二氯-苯基)-1,4-二氧杂-螺[4.5]癸烷-8-甲腈
• 英文名称: 8-(3,4-Dichlorophenyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile
• CAS: 65619-34-3
• 化学式: C₁₅H₁₅Cl₂NO₂
• 分子量: 312.196
• InChiKey: YOGISJQUYIXTKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(3,4-二氯-苯基)-1,4-二氧杂-螺[4.5]癸烷-8-甲腈 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇 为溶剂， 反应 30.0h， 生成 8-(3,4-dichlorophenyl)-N-methyl-1,4-dioxaspiro[4.5]decan-8-amine
  参考文献：
  名称：

  4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring

  摘要：

  Investigation of central nervous system activity of phenylcyclohexylamines was continued by preparation of "reversed" analogues. Following the unexpected finding of analgesic activity with 1-(dimethylamino)-1-phenylcyclohexylamine, the SAR of the series was investigated. Synthesis starts by double Michael reaction of acrylate on arylacetonitriles. Following cyclization, decarboxylation, ketalization, and saponification, the geminally substituted acid is rearranged to the isocyanate by means of (C6H5O)2PON3. Isocyanates were then converted to the title compounds. Analgesic activity is very sensitive to the nature and position of the substitutent on the aromatic ring. The most potent compounds in this series (p-CH3, p-Br) showed 50% the potency of morphine. Deletion of the ring oxygen abolishes activity.

  DOI：

  10.1021/jm00178a014
• 作为产物：
  描述：

  2-Carbomethoxy-4-(3,4-dichlorphenyl)-4-cyano-cyclohexanon 在 硫酸 、 对甲苯磺酸 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 30.0h， 生成 8-(3,4-二氯-苯基)-1,4-二氧杂-螺[4.5]癸烷-8-甲腈
  参考文献：
  名称：

  4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring

  摘要：

  Investigation of central nervous system activity of phenylcyclohexylamines was continued by preparation of "reversed" analogues. Following the unexpected finding of analgesic activity with 1-(dimethylamino)-1-phenylcyclohexylamine, the SAR of the series was investigated. Synthesis starts by double Michael reaction of acrylate on arylacetonitriles. Following cyclization, decarboxylation, ketalization, and saponification, the geminally substituted acid is rearranged to the isocyanate by means of (C6H5O)2PON3. Isocyanates were then converted to the title compounds. Analgesic activity is very sensitive to the nature and position of the substitutent on the aromatic ring. The most potent compounds in this series (p-CH3, p-Br) showed 50% the potency of morphine. Deletion of the ring oxygen abolishes activity.

  DOI：

  10.1021/jm00178a014

文献信息

• LEDNICER D.; VOIGTLANDER P. F.; EMMERT D. E., J. MED. CHEM., 1980, 23, NO 4, 424-430
  作者：LEDNICER D.、 VOIGTLANDER P. F.、 EMMERT D. E.

  DOI：——

  日期：——
• PYRROLIDINE TRIPLE REUPTAKE INHIBITORS
  申请人：Shao Liming

  公开号：US20120022125A1

  公开（公告）日：2012-01-26

  In various embodiments, the present invention provides cycloalkyl pyrrolidine compounds and methods for their use in the treatment and/or prevention of various diseases, conditions and syndromes, including central nervous system (CNS) disorders, such as depression, anxiety, schizophrenia and sleep disorder as well as methods for their synthesis. The invention also relates to pharmaceutical compositions containing the compounds of the invention, as well as methods of inhibiting reuptake of endogenous monoamines, such as dopamine, serotonin and norepinephrine from the synaptic cleft and methods of modulating one or more monoamine transporter.
• US8389559B2
  申请人：——

  公开号：US8389559B2

  公开（公告）日：2013-03-05
• US8754117B2
  申请人：——

  公开号：US8754117B2

  公开（公告）日：2014-06-17
• US9056830B2
  申请人：——

  公开号：US9056830B2

  公开（公告）日：2015-06-16